Ultimate List of 250+ Questions Answered by Gary Vaynerchuk on the Ask Gary Vee Show

In honor of Gary Vaynerchuk’s 50th episode we bring to you the ultimate list of all of the questions Gary Vaynerchuk has answered on his Ask Gary Vee Show through the first 50 episodes.

We have wrote a post on every episode on our blog since he first started his YouTube show 4 months ago and every link below is a direct link to him answering each question on his YouTube channel directly.

We included two of the “remix” videos as well and have counted over 250 questions (251 to be exact) he has answered in that 4 month period starting Jul 31st, 2014 when he posted his first Ask Gary Vee Show episode.

00:24 – When is the long tail actually just moving the goalpost?2:22 – How do you make your market embrace 2014 marketing tools when it’s really behind.4:07 – What’s the best way to grow your Pinterest and YouTube Followings by using Facebook Dark Posts?4:48 – What type of owner will you be when you own the Jets?5:24 – How do you translate your social media marketing wisdom into the world of music?5:58 – What’s the best way to gain real estate buyers’ trust?6:46 – How do I use social to promote a non-profit that doesn’t sell a product?

0:19 – How do I create interesting content for a boring subject like a hardware store?1:18 – How do I get the first 10 customers for a creative service startup?2:20 – I’m taught that people are basically sheep. How does this fit with your idea of “the customer decides”?3:18 – I’m a music producer. How can I use social to promote my content?6:13 – Where are the best places to hire great employees these days?

0:58 – What are the most important lessons your father taught you about building a business?2:10 – Where do you see yourself in five years?3:37 – What wine bars do you recommend?4:24 – How should I market a local social startup?5:51 – What’s your advice for small business owners with limited cash?

0:36 – For social media is it better to self brand or establish a brand?1:37 – How important is it that your significant other share your entrepreneurial vision?3:41 – What’s the most common mistake founders make building a consumer focused business?5:26 – Whats the biggest lesson you’ve learned this year?6:28 Whats the best advice you can give salespeople in the social media/digital world age?

00:35 – What are your thoughts on starting to share content before you are an expert? do you wait?02:09 – When you left the daily grape was it for Misha or Vaynermedia?02:41 – How do you change the culture to one of “genuinely caring” about the customer?03:46 – How do you book speaking engagements when you aren’t well known yet.04:42 – Since you published Crush it, what changes have you seen on online content creation? and how can people maximize it?

0:27 – What’s the best way to use Facebook dark posts?1:51 – Is it still necessary to drive traffic from social to your dot com?3:57 – How’d you deal with working in a family business?5:03 – What did you think of the Dalton trade?5:38 – Does the demand for your attention get overwhelming?6:20 – If you had to do it over again, would you start with WLTV, or Wine Library?

1:58 – Who are your idols? or the people that inspire you?2:58 – Should I take a risk by expanding to other platforms? or stick to youtube?4:05 – What do you consider more valuable…enthusiasm or action?5:36 – How would you suggest an indie artist use their marketing money when royalty checks come in 6 months later?6:25 – Cake or Pie?6:39 – Any tips on how to make an unknown hashtag popular?

0:39 Do you believe in Jim Collins belief that we can only focus on 3 things?1:38 What is the best way to grow a following or community from nothing?3:36 Tea or Coffee? or wine?3:57 As a business leader whats one thing that keeps you up at night?4:54 Center or Edge?5:01 What’s the best way for a right hook to seem like a jab?7:26 How can public institutions/government use social media more effectively in marketing campaigns?

00:42 – What’s an area of life you haven’t given your fullest efforts?02:16 – How does humor play a role in business…if at all?03:37 – Is JJJRH coming out in audiobook form?04:56 – (Part 1) What’s the hardest thing to deal with in the past 5 Years? How’d you get through it?05:18 – Michaels Bucket Challenge05:52 – (Part 2) What’s the hardest thing to deal with in the past 5 Years? How’d you get through it?07:29 – How do you start with funding of a billion dollar business plan when you have no financial resources?

01:25 – Do you ever complain? whats your attitude towards complaining?03:25 – I’ve been doing a lot of jabbing, but I don’t feel like I’m hitting anything, any advice?04:59 – How do I get the cute old lady who keeps calling my house to stop?05:37 Is it better to update your social networks once a week with great content, or daily with poor content?06:30 – How much of success is confidence, skill & luck?08:27– Do you think Facebook is effective? even though it’s pay for play?

00:44 – If you owned a winery in Napa, what would your left jabs look like?03:24 Do you respond to your post/tweets/emails/messages personally? or do you delegate?04:52 What foods have you added to your lifestyle that you are enjoying the most?05:23 How can I converge my vision of being a youtuber, while my parents want me to go to college?05:49 What are your thoughts about FB banning like-gating soon?07:06 – Do you think Reddit is a social media? do you find it useful?

0:32 – As a freelancer, should you ever work for “exposure” only?2:52 – Is it worth it to pay to promote your social content if it’s not getting enough engagement?4:33 – What’s the last new skill your learned as a product of taking an interest in someone else’s passion, hobby, or job?5:40 – When you’re in a funk, what do you do to get out of it?9:00 – How do you deal with the “low” that comes after the huge high you get from doing events and conferences?11:37 – What has your brother AJ learned from you and applied in business?

00:20 – What’s the fastest way someone can piss you off?01:12 – How do I use Snapchat for a winery?03:00 – How do we maintain our intimate customer experience with growth?04:28 – What’s better for content? vlogging? or blogging?05:53 – How do I present my consultant services to a potential client?07:59 – How do you determine you are creating valuable content?

00:36 – What roles does internal culture play in the company’s success? Can you give 1 concrete tip on building that culture?02:15 – Have you read any books changed your life in a very positive way?03:50– What were the 3 most effective things you did to drive book sales?06:16 – Do you see a parallel between Tennis and Business?09-40: What situations do you find yourself most comfortable in?

00:27 – What would you do if you were in your dad’s shoes and didn’t come to the US until you were 23+?01:13 – You say you focus on top line versus bottom line, why?02:44 – Do you believe in Pareto’s Principle?04:31 – What have you gotten out of the #ASKGARYVEE show?

0:26 – What do you think about the Apple Watch?1:32 – Is the personal website going to continue to be relevant, or should I look into something like building an app?3:08 – Do you set and track personal/business goals?4:19 – What was the riskiest thing you’ve ever done in your career?

01:33 – If you could market on only one platform, which one would it be and why?03:23 – As we go from concept to final product, what is the best way to empower our readers to spread the word?05:52 – Whats your process for vetting clients – specifically Vaynermedia?07:22 – How do you get away with dropping the F-Bomb?09:32 – What was the hardest thing when starting Vaynermedia?

0:35 – What media do you consume?02:33 – Should I still pursue marketing?04:15 – How do you feel about your impact on others?06:02 – Do you speak russian?06:54 – How do I make sure lack of confidence doesn’t stop me from chasing my dreams?08:38 -How do I take my video blog to the NEXT level?

00:40 – What wine pairs with kimchi?01:44 – Why do you release ASKGARYVEE during the evening? trying to target East Coasters?02:40– How do you prepare for a keynote?03:57– Do you think any of your areas of expertise hold you back from innovating?05:28– What am I doing wrong between my personal instagram account and the one I run for my company?

00:33 – I find it difficult to accept that men use Pinterest. Any way I can overcome this bias?01:26– How do you go around letting a business run their new social media plans themselves?03:19– How do I convey what a following is to teachers/head of schools etc?05:46 – Gary being the frontman of VaynerMedia. How do you manage your clients expectations to meet you?07:00– Guys seem to outnumber women on the show. Do you see men and women differ on success and tactics?

00:35– What is your best tip for time management?02:01 – Why are you uploading #ASKGARYVEE directly to Facebook instead of attaching a photo and linking it to your website? (or youtube?)03:09 – How should I start promoting my app 6 months before?05:00– If you could teach everyone in the world one thing you’ve learned what would it be?06:56 – If you could go back to your 20’s would you prioritize your health more? or was neglecting it necessary to get where you are today?

00:38 – If you bought the Jets today, what would be the first thing you would do?01:18– What motivates you to continue to any project (like wine library) without seeing any significant growth prior?02:08 – As an entrepreneur how do you feel about gov officials picking winner i.e Wynn getting approval for casino in Boston?03:13– What is your response to brands looking for 24/7 community management? Is it worth the investment or overkill?04:14– Do you trust that with enough good will and trust people will find your website/email when it’s time to buy? If I need my content to drive bookings, should I at least have a link for more info, when people are ready for it?

00:39 – Should I post articles on my blog and mention on social or post natively on sites like Linkedin, Medium, FB? or both?03:02 – You always answer business related questions, but what is 1 life lesson you have learned since becoming a father?05:22 – What do you think about Instagram integrating advertising?07:35 – If the Jets were never come up for sale in your lifetime, and another NFL team does, would you buy it instead?08:08 – How would you promote a kickstarted campaign beyond providing content to raise awareness and reach funding goal.

00:39 – Which hurts your credibility more: having no popularity or faking your popularity? Thoughts on fake views, plays, etc?01:36 – Would you ever automate your position, delegate to as many people as it takes and spend 95% of your time to fully engage in family and life?02:58 – When you get the occasional rushes of inspiration and motivation and it disappears, how do you get constant motivation?07:03 – Why is your phone always in the shot?07:51 – What are your thoughts on tech consumption by young children?

00:33 – What do you look for when hiring creatives?01:43 – You’re like a billionaire right? What do you splurge on?02:45 – Pre-Season hockey is on, if you owned a hockey team what would you do with snapchat?04:25– How do you generate novel ideas in an overpopulated seemingly stale industry? (the fitness industry in my case)05:53 – With the NFL in London this week, what do you think about sports franchises moving to different cities or countries?

01:11– Do you suggest that small businesses should become media companies?03:34– Should people quit trying to better their weaknesses?05:50– What should you do if you are an entrepreneur and have a full time job?08:07– How do you make it happen as an entrepreneur? even when you are older?11:55– How do you execute when you are afraid to fail?

00:37 – It seems like Instagram is great for jabs, not for right hooks. How and should I make right hooks on instagram or is it a bad idea all together?02:52 – What are your thoughts on using kickstarted to start a business?04:18 – Is there a thing as too much jabbing? or should you hold a little back to seem mysterious?07:25 – Is there a strategy behind following thousands of people on twitter? I normally follow those who provide value to me.09:37 – What are your thoughts on Ello?

01:18 – With the influencer business model, what are the biggest challenges are you facing? and which brands are using the influencer model.03:19 – How do you maintain having high standards with your team and making sure things get done, while keeping the project on time and in budget?04:50 – What do you think the next/biggest thing in the influencer space?06:29 – When startups become inherently competitive with other companies, how do you stay ahead of the game? give more value than your competitors?08:58 – What’s your stance on investing in competitive companies?

01:02 – What do you think about recent Omnicom advice to move 25% of ad budgets to online video and the space in general?03:20 – What’s a good drinking-home-along-bottle-to-yourself-w­ine?04:30 – You talk about upcoming companies and predicting their success or not. Where and how do you find these rising companies?

00:36 What is your opinion on listicle sites and posts?02:57 In the age of social media, twitter, vine and instagram length. How does/should this affect a startup in choosing a name?04:52 When you left Wine Library to start Vaynermedia, was it a conscious decision not to have someone take over Wine Library TV

01:44 – I’m a self taught social media marketer – is it worth doing a course on it, for applying jobs?03:32 – How many impressions do you or your tweets have?05:26 – Back in the old days of hiphop were you East Coast or West Coast? or both?06:01– Short versus long videos?07:38 – What is your take on marketing automation Software? How can you automate and still be human?

2:15 – Do you think it’s possible to hustle like you do anywhere outside the USA?3:28 – What are your thoughts on people who say things like Twitter, Uber, and Snapchat are overvalued?5:26 – For a blog that’s just starting out, how do I get people to do interviews with me even though I’m not a big-name media company?7:37 – What do you do if you have unique content, but you’re not tapping into the right audience or gaining visibility?8:22 – At what point do you get rid of a client because they’re just a jerk?

01:04 – We have high school kids working to get recruited and play college gold – suggestions on social responsibility on social media?03:05 – How do very new and small channels gain a following when people don’t interact and we get like 5 views on our video and 3 from us?06:51 – Who is your favorite comedian?07:41 – Sometimes my passion is seen as aggression, how do I walk the line? Do I change to someone more passive?10:24 – If it wasn’t for the 14th amendment, would you run for president?

00:35 – Can I add curated content to my own content? if yes, what’s the right mix?03:37 – How much sleep do you get on average? Do you work 7 days a week? Do you have set days off to spend time with family?05:50 – What have you found is the best way to introduce non wine drinkers to wine without seeming overwhelming?07:44 – I know marketers ruing everything but is twitters latest algorithm change going to damage the user experience and the essence of twitter?11:02 – What would you do if you were starting over and building your personal brand? how would you start the @garyvee brand if you had to do it all over?

01:02 – As an email marketer, I say email is not dead. Do you think email will be more or less relevant in 3-5 years?03:07 – I work in two different spaces. How do I use social media platforms so I am not confusing my audiences?04:58 – How do you define hustle?06:51– What do you really get from having 10,000 followers?11:57 – A professor once said to me, It’s better to be a big fish in a small pond? Do you agree?

00:28– Would love to hear your opinion on whether a PR company or person should be overseeing #socialmedia for business.02:14 – What was the moment you knew you would be “okay” when starting your business?04:04 – Is there a way to drive traffic to a website when posting content directly to Facebook?05:43 – You said it’s important to put out daily content. As a realtor what kind of daily video content would you produce?07:48 – Most big success have a huge turning point where things really take off. What was that turning point for Winelibrary

00:29 – Take us back to the day when you said yes to @JeromeJarre. What made you believe in him and his idea?03:11 – What is your opinion on the auto-reply DM services people use to send a message to new followers on twitter?04:58 – When have you been the happiest in your life?07:52 – How can you stand out in linked in with all the chatter from social media gurus that are spamming everyone’s feed?11:05 – Sup?

01:05 – Can anyone create good micro-content? How can you make sure your team consistently creates good content?04:19 – What are your thoughts on podcasters and YouTubers building a business model around donations?06:43 – What’s up with virtual reality?09:18 – I know you hate talking about ROI but how do you show someone there is a true return on your efforts on social media?13:28 – What do you feel is a bigger obstacle question to success a lack of time or a lack of capital?

00:51: With Facebook reach continuing to decline, do you see a role for organic posts as an ‘always on’ strategy or should everything be promoted? How much reach is enough to justify the effort in creating these assets?04:19: What dating advice would you give to a single 20-something girl in NYC?08:22: At what point is a campaign ownable by merely being the first brand of its kind to do something (in a sense being the “first mover”)?11:30: What’s the most important thing you’ve learned while Vayner has grown as a company (from coast to coast) and how does a company successfully scale?14:57: What kind of advice would you give people who are transitioning from the do-ers to the leaders and managers of a team?

00:33 – I like how you talk about execution in business, how do you prioritize which project to execute first?01:42 – Before you had an assistant, how did you structure your day?02:59 – If you were to jump into a time machine, travel back to speak to your 21 year old self, and only have 1 minute. What do you say?03:43 If your dad Sasha would have ended up in construction how do you think it would affect your life, without wine library?

1:10 – What are your pet peeves? and what skill do you wish you were better at?03:43– What ways can agencies make staff meetings more productive?05:21– I am a 14 year old, I want to be an entrepreneur..but I don’t know where to start? What actions should I be taking as a kid?07:10 – As a fellow son of immigrants when you were 25 how did you overcome fear of not doing as much or not having it as hard?10:04 – What social media techniques do you think work best when promoting a book?

00:33 – Why do you rarely recommend youtube in your digital recommendations despite the 1 billion active users per month.02:25 – You changed the intro music why?02:34 – What’s one question you ask in interviews04:36 – As a private music teacher I have limited hours to teach. Thoughts on how to increase my income/brand?

00:50 – Shark Tank’s Corcoran doesn’t invest in “rich kids” businesses. How do you feel about entrepreneurs from privilege?03:22 – How long is Gary going to make us wait for the “Heart to Brain to Wallet” t-shirt he teased in EP. 41 of #AskGaryVee

01:19 – Airbnb goes into print, they are making a magazine called Pineapple02:31 – Do you still the Thank You Economy will self destruct in 2015? Are brands living up to your prediction/TYE expectations?04:03 – In the future how are you going to treat social media with your children?07:10 – Everybody asks what do you think of Snapcash?

00:51 – What trends should brick and mortar stores be paying attention to over the next 12 to 18 months?03:20 – With all the talk about #Snapcash what is the one thing you’ll teach your kids about money?04:30 – How much of my advertising marketing dollars, should I spend on salespeople or telemarketing? vs direct mail, print and traditional marketing? vs online?07:45 Do you script answers or improvise? How much time do you invest in prep and production per show?09:16 – Can you explain in more detail your statement from @marketmakers that Superbowl-ads are underpriced?

01:23 – How many “punches in the face” & failures can an ordinary person handle before achieving success?03:07 – Any tips on how to get a mentor?06:47 -What was the biggest decision in your life that made you successful today?09:27 – Is paid promotion for “jabs” an effective way to build audience for “right hooks” down the line?11:26 – Do you schedule time to be on social media? or just jump on randomly during the day as you have time?

01:27 – Should I wait until my website is 100% built before putting out content or put out content while I’m still building it?03:08 – How would you recommend looking for a co-founder05:04 – I have my own blog, but I don’t do podcast or videos because I have a Russian accent, and I worry about my trustworthiness is this something I should worry about?08:16 – In the past what was your equivalent of that #OneAlmond moment from episode 46? What did you potentially miss out on?10:59 – What’s behind the recent big surge in wine time for you? Missing it? Big opportunity in app?

01:44 – How much time should you spend on your competition? Or should you just be focused on making your own path?03:30 – Who would you recommend pitching an app idea to? What steps would you recommend?05:48 – Niche marketing, in wine library did you market to people interested in wine? or specific niches in the wine community?07:36 – What would you do if all 420 employees quit vaynermedia?11:02 How do you instill soul and swagger into a physical product you create?

1:41– What came first at Vaynermedia: clients or employees? (And did you ever do stuff without employees?)3:51– Do you have any bucket list items that you want to complete before 40?4:57– Is the high end wine business a complete hoax?7:47– How do you “not procrastinate” that well?11:33 – How exactly did your mother instill that self-confidence in you?

02:24 – If you don’t care about the competition, what do you say when a client asks you about a competitor and why you’re better?04:02 – White lies, do you believe the hype? It seems you can’t win in business without bending the truth?06:40 – Is the lack of chairs in your office a part of instilling the hustle in your employees?08:29 – I saw a discussion via Linkedin about Klout scores on a resume. What are your thoughts on them?10:47 – Are there any common mistakes that you repeat over and over again? Any tips on overcoming them?

[…] vayniacs ask him questions about business, life, family, and social media. It’s called the Ask Gary Vee Show and the foundation to an upcoming book and where he gives away free value (jabs) until he is ready […]